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Trigonelline

$43

  • Brand : BIOFRON

  • Catalogue Number : BF-T2003

  • Specification : 98%

  • CAS number : 535-83-1

  • Formula : C7H7NO2

  • Molecular Weight : 137.14

  • PUBCHEM ID : 5570

  • Volume : 20mg

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Catalogue Number

BF-T2003

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

137.14

Appearance

White crystalline powder

Botanical Source

seeds of Trigonella foenum-graecum L.

Structure Type

Alkaloids

Category

Standards;Natural Pytochemical;API

SMILES

C[N+]1=CC=CC(=C1)C(=O)[O-]

Synonyms

Betain nicotinateTrigonelline/N-methyl-3-carboxypyridinium/Gynesis/Coffearine/Gynesine/Pyridinium, 3-carboxy-1-methyl-, inner salt/Trigenolline/1-methylpyridinium-3-carbonate/Nicotinic acid N-methylbetaine/1-methyl-3-pyridinium carboxylate/1-Methylpyridinium-3-carboxylate/Pyridinium, 3-carboxy-1-methyl-, hydroxide, inner salt/Pyridinium, 3-carboxy-1-methyl-, hydroxide, inner salt (8CI)/Caffearine/1-Methyl-3-pyridiniumcarboxylate/Trigonellin/Coffearin/N-Methylnicotinate

IUPAC Name

1-methylpyridin-1-ium-3-carboxylate

Density

1.2528 (rough estimate)

Solubility

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

Flash Point

Boiling Point

251.96°C (rough estimate)

Melting Point

260ºC (dec.)

InChl

InChI=1S/C7H7NO2/c1-8-4-2-3-6(5-8)7(9)10/h2-5H,1H3

InChl Key

WWNNZCOKKKDOPX-UHFFFAOYSA-N

WGK Germany

RID/ADR

HS Code Reference

2933390000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:535-83-1) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

31841988

Abstract

It has been widely reported that ultraviolet-B (UV-B) radiation is the main extrinsic etiological agent that causes skin photodamage. UV-B exposure mediated photodamage (photo-aging/photo-carcinogenesis) to human skin is caused due to several physiological events at tissue, cellular and molecular levels that lead to impairment of skin function and integrity. In the present study, we investigated the protective role of Trigonelline (TG) against UV-B induced photo-damage in Human Dermal Fibroblasts (Hs68 cells) and Balb/C mice. We exposed human skin fibroblasts and Balb/C mice to UV-B radiation and evaluated various parameters of cellular damage, including, oxidative stress, cytosolic calcium (Ca2+) levels, apoptotic and ER-stress marker proteins. We found that UV-B irradiation induced ROS generation lead to the depletion of endoplasmic reticulum (ER) calcium and increased the expression of ER stress protein markers (phosphorylated elf2α, CHOP, ATF4) as well as apoptotic protein markers (Bcl2, Bax and caspase-9) in a dose and time dependent manner in Hs68 cells. We then determined the effect of TG treatment on UV-B -induced cell death in Hs68 cells and observed that cells exposed to UV-B radiation and treated with TG had a significantly higher survival rate compared to cells exposed to UV-B radiation alone. TG treatment successfully reduced oxidative stress; restored Ca2+ homeostasis and re-established the ER function and prevented apoptotic cell death process. Our results suggest that TG can be used as a potential therapeutic/cosmeceutic agent in preventing skin photo-damage.

Copyright © 2019 Elsevier B.V. All rights reserved.

KEYWORDS

Calcium homeostasis; ER-stress; Oxidative stress; Photodamage; Trigonelline; Ultraviolet B

Title

Trigonelline, a naturally occurring alkaloidal agent protects ultraviolet-B (UV-B) irradiation induced apoptotic cell death in human skin fibroblasts via attenuation of oxidative stress, restoration of cellular calcium homeostasis and prevention of endoplasmic reticulum (ER) stress.

Author

Lone A N1, Malik A T1, Naikoo H S1, Raghu R S1, A Tasduq S2.

Publish date

2020 Jan

PMID

31669600

Abstract

Fibrogenesis is a common feature for all types of chronic kidney disease (CKD). Epithelial-to-mesenchymal transition (EMT) of renal tubular epithelial cells is one of the main processes involving renal fibrosis and its inhibition is considered as a preventive/therapeutic strategy for CKD. Trigonelline (TRIG), a plant alkaloid commonly found in herbs, coffee bean, soy bean and other edible food plants, has several beneficial effects on human health and has been proposed to reduce renal fibrosis but with unclear mechanisms. This study thus addressed cellular mechanism underlying the anti-fibrogenic effects of TRIG in renal tubular epithelial cells grown in vitro. EMT was successfully induced by oxalate treatment as indicated by morphological changes into spindle-shape cells, increased expression of mesenchymal proteins (fibronectin, vimentin and α-smooth muscle actin (α-SMA)), decreased expression of epithelial proteins (E-cadherin and zonula occludens-1 (ZO-1)) and increased activity of a profibrotic factor (matrix metalloproteinase-9 (MMP-9)). Interestingly, these oxalate-induced EMT features could be attenuated by TRIG pretreatment. Moreover, TRIG also prevented oxalate-induced cell migration, reactive oxygen species (ROS) overproduction, and down-regulation of Nrf-2 signaling molecule. These data indicated that TRIG could attenuate the effects of oxalate-induced EMT and thus may serve as the anti-fibrotic compound for prevention and/or treatment of CKD.

Copyright © 2019 Elsevier Ltd. All rights reserved.

KEYWORDS

CKD; E-cadherin; EMT; Fibronectin; MMP-9; Nrf-2; ROS; Renal fibrosis; Spindle index; Vimentin; ZO-1; α-SMA

Title

Protective roles of trigonelline against oxalate-induced epithelial-to-mesenchymal transition in renal tubular epithelial cells: An in vitro study.

Author

Peerapen P1, Thongboonkerd V2.

Publish date

2020 Jan

PMID

31291287

Abstract

Linden (Tilia spp.), a profusely flowering temperate tree that provides bees with vital pollen and nectar, has been associated with bumble bee (Bombus spp.) mortality in Europe and North America. Bee deaths have been attributed, with inadequate evidence, to toxicity from mannose in nectar or starvation due to low nectar in late blooming linden. Here, we investigated both factors via untargeted metabolomic analyses of nectar from five T. cordata trees beneath which crawling/dead bumble bees (B. vosnesenskii) were observed, and of thoracic muscle of 28 healthy foraging and 29 crawling bees collected from linden trees on cool mornings (< 30°C). Nectar contained the pyridine alkaloid trigonelline, a weak acetylcholinesterase inhibitor, but no mannose. Principal component analysis of muscle metabolites produced distinct clustering of healthy and crawling bees, with significant differences (P<0.05) in 34 of 123 identified metabolites. Of these, TCA (Krebs) cycle intermediates were strongly represented (pathway analysis; P<0.01), suggesting that the central metabolism is affected in crawling bees. Hence, we propose the following explanation: when ambient temperature is low, bees with energy deficit are unable to maintain the thoracic temperature required for flight, and consequently fall, crawl, and ultimately, die. Energy deficit could occur when bees continue to forage on linden despite limited nectar availability either due to loyalty to a previously energy-rich source or trigonelline-triggered memory/learning impairment, documented earlier with other alkaloids. Thus, the combination of low temperature and nectar volume, resource fidelity, and alkaloids in nectar could explain the unique phenomenon of bumble bee mortality associated with linden.

Title

Linden (Tilia cordata) associated bumble bee mortality: Metabolomic analysis of nectar and bee muscle.

Author

Lande C1, Rao S1, Morre JT2, Galindo G1, Kirby J1, Reardon PN3, Bobe G4,5, Stevens JF4,6.

Publish date

2019 Jul 10


Description :

Trigonelline, an alkaloid with potential antidiabetic activity, is present in considerable amounts in coffee.